We may receive a commission if you make purchases through affiliate links (at no extra cost to you). Read why our approach to travel is different.
There are plenty of places you can spend Christmas, but very few of them deliver on those festive Christmassy vibes as well as Chicago does. The de facto American Midwest, Chicago is the home of some of our favorite Christmas movies, festive events and year-round attractions. And with almost a meter (37”) of snow falling each year, you are (almost) guaranteed a white Christmas.
Chicago delivers the best of what makes Christmas so special. There’s markets, lights, snow, theater performances, places to roast s’mores, and a seemingly unending selection of events (for both children and adults). So pack your warmest clothes (you’ll really want your thickest jackets) and spend Christmas in Chicago.
Skip to...
Make time for lights at Lincoln Park Zoo
Assuming you’ve packed appropriately, the Lincoln Park Zoo Lights are an all-time favorite of locals and visitors alike. Easily accessible by public transport, Lincoln Park Zoo is in the heart of the city. For 30 years, they’ve drenched the place in over three million Christmas lights (yes, 3,000,000).
Festivities run from mid-November through New Year – you’ll find carolers, cookie decorating, ice carving, a ferris wheel (highly recommended as the views of the Chicago skyline are truly magnificent) and up until December 23 you can visit Santa and drop off your Christmas list. (Santa has a deadline of Christmas Eve for gift requests, apparently.)
If you need to warm up along the way, there’s plenty of hot chocolate and open fires for roasting s’mores. Tickets are essential and the event is free on select Mondays.
If you’re still feeling tough enough to brave the outdoors, don’t miss the opportunity to go ice skating in Millennium Park, right next to the iconic Cloud Gate sculpture (fondly known as The Bean). There are a lot of beginners out there, so don’t worry if you’re a bit wobbly. You’ll need to book in advance and you can rent skates on site.
Warm up with a hot chocolate afterwards and enjoy a mulled wine or a snowball at the Chicago Athletic Association across the street. Alternatively, you can slip and slide your way down the skating ribbon – a path that winds through Maggie Daley Park (it’s a bit longer and just next to Millennium Park).
See the Second City Christmas Show
Hands down my personal favorite Christmas in Chicago tradition is the annual Second City Christmas Show. The Second City is a bona fide Chicago institution, a first-rate improv theater with a distinguished alumni list that includes Bill Murray, Stephen Colbert, Steve Carrell and Tina Fey. Be ready to laugh (and potentially be summoned on stage – anything can happen, just ask my brother-in-law!)
It’s old school comedy club vibes with random seating and stellar table service. If your show is on the Second City mainstage (they have venues across the city) head across the street to the Old Town Ale House after the show. One of Chicago’s finest drinking establishments, this old-school dive bar is cash only and was a favorite haunt of celebrity food presenter Anthony Bourdain. Be prepared for the controversial portraits of famous figures on the walls.
Nutcracker, Chicago style
If you’re looking for something more refined, don’t miss the Joffrey Ballet’s Nutcracker. This version has a special Chicago twist – it is set on the fairgrounds of the 1893 World’s Fair which, of course, was hosted in Chicago. It’s a world-class performance and the venue is the stately Lyric Opera House, an Art Deco masterpiece and one of Chicago’s finest (of many) theaters.
Join the sing-along at the Music Box Theater
The annual Christmas sing-a-long at the Music Box Theater is a beloved local tradition. You’ll be greeted by Santa and then join the audience to belt out your favorite Christmas tunes accompanied by a live organ (lyrics are shown on screen, just in case you’re a bit rusty).
After you’ve had your fill of singing, sit back and enjoy the Christmas classic It’s a Wonderful Life and, if you want to make it a double feature, stay on for another round of carols and sing-a-long with Bing Crosby and Rosemary Clooney in White Christmas.
This vintage theater is full of charm and has a cozy lounge. Order the Chicago Handshake and take the opportunity to sample Chicago’s most notorious adult beverage, Malort. Generous descriptions would say Malort has herbal undertones with a bitter finish – other descriptions have included burnt tires and bug spray. Try at your own risk.
Visit the Home Alone house
Another one for the cinephiles among us. Head north to the swanky suburb of Winnetka, specifically 671 Lincoln Avenue where you’ll find the iconic Home Alone house. The home is a private residence, but so long as you respect the privacy of the current owners (please don’t knock on the door), you can snap a selfie. Don’t forget to practice your Kevin McAllister scream face!
The Christmas exhibition at the Museum of Science and Industry
The Museum of Science and Industry is well worth a visit on it’s own merits (there’s a real WWII German submarine, a coal mine and lots of stuff for space nerds) but each year the museum hosts a Christmas Around the World exhibit which features 50 Christmas trees representing different cultures and celebrations from across the globe.
It’s a great family activity and even the grown ups will be impressed by the four-storey main tree. Access to the exhibit is covered with general admission – so make a day of it.
If you’re strolling down Michigan Avenue (aka the Magnificent Mile), snap a selfie with the stately lions (adorned with Christmas wreaths) at the Art Institute of Chicago. The museum itself is one of the finest in the United States. You’ll find iconic paintings like Grant Wood’s American Gothic and Edward Hopper’s Nighthawks and there’s Chagall’s luminous America Windows.
If you have the kids in tow, the miniature rooms and medieval armory collections are always a hit.
Christmas Market, Chicago-style
Attracting over one million visitors each year and considered to be one of the best Christmas Markets outside of Europe, the Chicago Christkindlmarket has gained a worthy international reputation. Cruise around with a mulled wine (the annual souvenir mug has become a favorite keepsake) and enjoy live dance and music acts.
You can of course browse beautiful handmade glass ornaments, wooden figurines and countless decorations and trinkets. It kind of looks a lot like a European Christmas market, but it very much has its own Chicago edge (Americans can make sausages even bigger than the Germans).
Come hungry to fill up on hearty traditional German(ish) fare including bratwurst, pretzels, perogies, schnitzel and raclette (this is the one to try). It is positively heaving on the weekends, so do visit on a weekday if you can. If you really want to beat the crowds, aim for midmorning.
For the Armchair Traveler
Chicago is the backdrop for two of the greatest Christmas movies of all time – National Lampoon’s Christmas Vacation and Home Alone. For a fun-filled Christmas in Chicago night in, snuggle up with a deep dish Chicago-style pizza and get a few Chicago craft beers – Goose Island, Half Acre Brewing Co and Revolution all got their start in Chicago.
Share This Article
Traveling soon? Subscribe to The Insight below and get exclusive access to our personalized travel advice community via WhatsApp so you can ask all your burning travel questions.
Looking for the best comprehensive travel insurance? SafetyWing has you covered.
And for your eSIM in every country, there is only one option we recommend: Airalo.
Read more of our best insights from around the world
- A Flying Visit to Sin City: One Day in Las Vegas
- 10 Best Restaurants In Pattaya: Fine-dining, Views and Beachfront Locations
- The Perfect 10 Day Itinerary for Türkiye: History, Culture and Sea
- 6 Best Restaurants in Prenzlauer Berg, Berlin for 2025
- 7 Best Things To Do In Pattaya: 2-Hours From Bangkok!
- Helsinki vs. Stockholm – Deciding Which Baltic Sea Capital to Visit
